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. 2017 Feb 8;139(5):1774-1777.
doi: 10.1021/jacs.6b12307. Epub 2017 Jan 27.

Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

Xiao-Hui Yang  1 , Vy M Dong  1
Affiliations

Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

Xiao-Hui Yang et al. J Am Chem Soc. .

Abstract

We communicate a strategy for the hydrofunctionalization of 1,3-dienes via Rh-hydride catalysis. Conjugated dienes are coupled to nucleophiles to demonstrate the feasibility of novel C-C, C-O, C-S, and C-N bond forming processes. In the presence of a chiral JoSPOphos ligand, hydroamination generates chiral allylic amines with high regio- and enantioselectivity. Tuning both the pKa and steric properties of an acid-additive is critical for enantiocontrol.

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Figures

Figure 1.
Figure 1.
Rh-hydride catalyzed hydrofunctionalization of unsaturated compounds
Figure 2.
Figure 2.
Reaction design for the hydrofunctionalization of 1,3-dienes
See this image and copyright information in PMC

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